N-type compound containing naphthyl[1,2]imidazole as well as preparation and application thereof

A technology of imidazole and compound is applied in the field of electroluminescent materials to achieve the effects of promoting equilibrium, determining molecular weight and single molecular structure

Active Publication Date: 2016-04-20
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, combining naphthalene[1,2]imidazole as an electron-withdrawing unit with other aromatic conjugated units to form a new type of n-type conjugated compound, which can be used as a fluorescent light-emitting molecule or electron transport material in organic light-emitting diodes, has so far been seldom There are reports

Method used

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  • N-type compound containing naphthyl[1,2]imidazole as well as preparation and application thereof
  • N-type compound containing naphthyl[1,2]imidazole as well as preparation and application thereof
  • N-type compound containing naphthyl[1,2]imidazole as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] The preparation of a kind of n-type compound 1 containing naphtho[1,2]imidazole of the present embodiment, the reaction formula is as follows:

[0030]

[0031] The specific preparation steps are: in a 250 ml single-necked flask, N'-benzene-1,2-diaminonaphthalene (12mmol, 2.8g) and terephthaloyl chloride (1.02g, 5mmol) were added to 100mL of dichloromethane Dissolved in , then added 2 ml of triethylamine, and reacted at room temperature for 10 hours. Then the solid precipitated in the reaction was filtered off, and rinsed with a small amount of ethanol and acetone successively. After the obtained white solid was dried, it was added into a 100 mL one-necked flask, mixed with 50 mL of acetic acid and heated to 110° C. for 12 hours. The mixture was then poured into 250 mL of water, and the product was extracted with dichloromethane. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed after separation. The white solid was separated...

Embodiment 2

[0033] The preparation of a kind of n-type compound 2 containing naphtho[1,2]imidazole of the present embodiment, the reaction formula is as follows:

[0034]

[0035] The specific preparation steps are: in a 250 ml single-necked flask, N-benzene-1,2-diaminonaphthalene (12mmol, 2.8g) and terephthaloyl chloride (1.02g, 5mmol) were added to 100mL of dichloromethane Dissolved, then added 2 ml of triethylamine, and reacted at room temperature for 10 hours. Then the solid precipitated in the reaction was filtered off, and rinsed with a small amount of ethanol and acetone successively. After the obtained white solid was dried, it was added into a 100 mL one-necked flask, mixed with 50 mL of acetic acid and heated to 110° C. for 12 hours. The mixture was then poured into 250 mL of water, and the product was extracted with dichloromethane. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed after separation. The white solid was separated and ...

Embodiment 3

[0037] The preparation of a kind of n-type compound 3 containing naphtho[1,2]imidazole of the present embodiment, the reaction formula is as follows:

[0038]

[0039] The specific preparation steps are: in a 250 ml single-necked flask, N'-benzene-1,2-diaminonaphthalene (12mmol, 2.8g) and 1,3,5-benzenetricarboxylic acid chloride (0.8g, 3mmol) were added to Dissolve in 100 mL of dichloromethane, then add 2 mL of triethylamine, and react at room temperature for 10 hours. Then the solid precipitated in the reaction was filtered off, and rinsed with a small amount of ethanol and acetone successively. After the obtained white solid was dried, it was added into a 100 mL one-necked flask, mixed with 50 mL of acetic acid and heated to 110° C. for 12 hours. The mixture was then poured into 250 mL of water, and the product was extracted with dichloromethane. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed after separation. The white solid was...

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Abstract

The invention belongs to the technical field of electroluminescent materials and discloses an n-type compound containing naphthyl[1,2]imidazole as well as preparation and application thereof. A preparation method comprises the following steps: carrying out a hydration cyclization reaction on a precursor of the naphthyl[1,2]imidazole and a conjugated aromatic unit, or carrying out a Suzuki coupling reaction on a halide containing the naphthyl[1,2]imidazole, or carrying out a ligand coupling reaction on a derivative of the naphthyl[1,2]imidazole and a metal compound to obtain the n-type compound containing the naphthyl[1,2]imidazole. The compound provided by the invention has a relatively high fluorescent quantum yield and electron transmission and electron injection capabilities, and relatively good solubility and film-forming property; the n-type compound can be applied to a luminous layer and an electron transmission layer in organic light-emitting devices including organic light emitting diodes and the like.

Description

technical field [0001] The invention belongs to the technical field of electroluminescent materials, and in particular relates to an n-type compound containing naphthalene[1,2]imidazole and its preparation and application. Background technique [0002] Organic light-emitting diodes (OLEDs) have broad application prospects due to their high efficiency, low-voltage drive, easy large-area preparation and full-color display, and have attracted widespread attention. The research began in the 1950s, and until 1987, Dr. Deng Qingyun of Kodak Company of the United States adopted a sandwich device structure in the patent US4356429, and the OLED device developed by the 10V DC voltage drive had a luminous brightness of 1000cd / m 2 , so that OLED has achieved an epoch-making development. Over the past two decades, OLED devices employing novel emitters, especially organic-heavy metal complex phosphorescent emitters, have achieved considerable success. However, due to the difficulty in o...

Claims

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Application Information

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IPC IPC(8): C07D235/02C09K11/06H01L51/54
CPCC09K11/06C07D235/02C09K2211/186C09K2211/188C09K2211/1007C09K2211/1011C09K2211/1044H10K85/615H10K85/626H10K85/30H10K85/381H10K85/324H10K85/6572
Inventor 苏仕健刘明李祥龙彭俊彪曹镛
Owner SOUTH CHINA UNIV OF TECH
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